I don't know who the hell I am to start throwing advice around about making LP's when I've never even tried to make one myself but, wtf, FWIW here's what I think:
The fundamental problem with DW is the combination of the huge scope of the game, the complexity of controlling your empire and the length of game play time it takes for things to happen such that the viewer gets some kind of idea what the hell is actually going on.
Another way to put this is that there are far too many things of too much complexity happening at once in too many places too fast for people who don't know anything about the game to follow but at the same time it takes a Youtube age and a half before any visible results from all this frenzied activity succeed in generating meaningful shifts in the galactic geopolitical situation, like the result of a war for example, so that the point of it all, the narrative, becomes clear to the viewer.
This makes making LPs of DW a big challenge, because there's a contradiction here: it goes too quick, but at the same time it goes too slow.
A possible approach to deal with this problem is to run three separate LP/walkthrough/tutorial series in tandem:
1. A full speed playthrough starting with the terran empire as in Veloxi's LP concentrating on broad sweep strategic issues and avoiding getting bogged down in any details of how or why you are doing specific low level tasks. The aim is to explain your overall objectives and the plan to achieve them at high level, give an overview of how you are going to execute that plan, and just play commenting on how well your plan appears to be succeeding or not. Let the story unfold, basically.
2. A pre-warp start playthrough concentrating on the details of system management, economy, ships and fleets, stations, resources, pirates and research as they affect the drive to escape the confines of your home system. The objective is simple and clear and this would leave plenty of space for commentary on the details of running an empire in miniature and demonstrate the interface.
3. A set of specific tutorial on various subjects, for example, ship/station design, resource acquisition, fleet management and combat, research, diplomacy and so on. These can be referenced in the commentary of the main walkthrough/LPs rather than go into those details there. Michael Broschek has done some excellent videos like this for Hearts of Iron 3 which are invaluable for new players. here's an example:
Another approach is the one taken by CdrDave (David Downer) in his walkthrough series for X3:Terran Conflict. In this indispensable series he takes the viewer through a somewhat edited playthrough where he jumps to critical points to explain specific game mechanics in detail as and when the need for them arises. I can testify how well it works because i learned how the play X3 from this series myself.